I'm too green for it to have happened to me, but I'm sure it's happened. You go into a fight confident, only to realize that due to whatever circumstances, you've bitten off way more than you can chew. Tell a story when you found yourself, a member of your group, or the whole team, in such a deep-fried pickle.

So, in the first published 5E adventure, I am The Old White Death, final boss of this dungeon, coming flying in to take out these puny adventurers who dare enter my lair. As soon as I come into view, the following happens. An elf in a hooded cloak and martial arts wraps puts two arrows to the string, critting with one, which turn out to be Arrows of Dragonslaying. I use two of my legendary resistances to avoid that doing horrifying amounts of damage, but it's still a serious blow. Then, a mage fires off a lightning bolt, doing some fair damage and eating up my last resistance. When the next few people either do nothing or fire off light damage arrow attacks, I think I'm in the clear.

That's when the Sorcerer in the back, wearing the Black Dragon Mask, casts a Maximized Disintegrate on me. I fail the save.

At this point, I'm almost there, but I'm nearly dead and panicking. Turning around, I flee, trying to escape. As I do, I hear one of the adventurers cast a spell. It turns out it was Haste. On the Wood-Elf Monk.

The monk proceeds to run after me, his already insane speed doubled, taking two actions to chase me like a lightning bolt across this cavern, and proceed to attempt to ventilate me, which would have very nearly killed me if I hadn't managed to dodge the crucial killing shot. Nope. Nope nope nope nope nope.

Let's see... one time in a Star Wars game I actually decided to avoid getting caught alongside the rest of the party. I thought it was clever, the GM took it as "splitting the party" and we all know how well that goes.

In the end I faced off against a Dark Jedi or Sith Lord (I don't remember which, and this was around the time of the prequels so... yeah) and in order to get away, I kicked him as hard as I could in the groin. This was the system using "Force Points" and I burned one, rolling so well I actually broke through what was essentially his armor's nut cup.

He did not like me. When he finally caught up to me, I died, though technically I was killed by friendly fire right before he could off me.

So will it make it better or worse when I mention that I think the "friendly fire" was from my second character; though I don't think it was part of the regular rules, the GM had allowed the more experienced players to run two guys at once.

I knew my first guy was going down and going down hard, but that my second character could take the shot, sort-of avenge the first. That or it was a sweet lie I told myself to cope and after almost two decades, I can't remember the truth. XP

Currently (sorta) playing a campaign of the new Fantasy Flight Star Wars, and had something similar happen.

I'm playing as JOWAHN KENAR, Jedi Guardian, a man 'roided out the ass with Force physical boosts and brawling skill. We encountered a trainee Sith who was in no way ready for a knock-down-drag-out with the party, but the real gold came when she whiffed a lightsaber swipe at the unarmed Kenar.

Kenar, of course, just pulled his brass knuckles and rocked her in the teeth, because he's a badass like that.

In our latest Pathfinder adventure, our party was facing off against a pair of rakshasas. Aside from them being made of damned iron, our rolls were absolute crap. Our fighter got a critical fail and stabbed off his own pinky toe, and I failed my (obscenely high) will save to not be charmed by the male one. The only reason we both lived is because of a pair of revenants out for revenge.
The next combat was even worse. Single combat against another rakshasa that turned out later to be effectively level 9 against our level 5 group. The battle took three hours real time and two of us almost died. Horror campaigns, am I right?

Well, recently, in a Shadowrun game. We had walked down into an area to rescue some kidnapped children. And then the big bad revealed themselves, sort of, they used mind control of some sort to turn us against each other, or rather turn everyone against me. So, I got shot in the back a couple times, fortunately, I'm a possession mage with a high force spirit bound to me, and their bullets didn't even break through my hardened armor. So there the rest of the party was, staring their former ally down, whom they had just recently watched break a cybered up troll's back by crushing him with her bare hands, in an enclosed space.

My friends and I are running the Carrion Crown campaign in Pathfinder, each book of which is based on a horror theme. We were at the end of the fourth, based on HP Lovecraft. I play Chekyl, the tengu alchemist, and my friends are Sir Ahsum the dim but lovable paladin, Elsbeth the snarky half-elf witch, and Janeath the grumpy half-orc gunslinger. For the most part, we're pretty inexperienced at tabletop, but we've somehow managed to survive everything we've had thrown at us through luck, copious reliance on healing, or (in cases like Elsbeth casting a spell to possess a Colour Out of Space) doing things that are completely reckless and stupid and making them actually work.

We'd descended down into an underwater temple that had been a temple to Dagon, and the local equivalent of Deep Ones that had a deal going on with this cult we've been chasing after the whole game. It turned out, though, that the temple had been taken over by a third party, the Mi-Go.

In the context of the game, the Mi-Go are fungal aliens shaped like giant insects. They're also an entire race of Mengeles, traveling through space and conquering worlds to sadistically 'experiment' on. So, we find the cult's representative at the end of the dungeon, on a slab surrounded by Mi-Go. We fight the shroom-bugs, and our group is generally pretty inexperienced in a game like Pathfinder, so we were largely out of our usual resources. Chekyl was out of bombs, Ahsum was out of heals, Elsbeth is more crowd control than direct damage with her spells in the first place, and Janeath can deal fairly steady damage, but isn't always set up properly for the situation. All in all, we needed to take a little breather to heal up and finish the story.

Instead, the body of the cultist went all Las Plagas on us, his head exploding into a writing mass. Now, the body was strapped securely to the slab, so we didn't have to act immediately, but Sir Ahsum decided it was too scary and icky not to stab.

As it turned out, this was actually the final step in a sacrificial ritual intended to summon one of the dark spawn of Shub-Niggurath, Black Goat of the Woods With a Thousand Young, into the world so that it could call mommy to ravage the world. So not only are we drained of heavy attacks, but we're still badly banged up from the Mi-Go, and are now in a room with a giant tentacular monstrosity spawned from the fetid womb of an alien elder god.

A room topped with a crystal dome which was all that was standing between us and countless tons of water, and had recently been renovated with a considerable amount of Mi-go technology which Chekyl knew from past experience to be rather... temperamental.

It was time to get reckless and stupid.

Dodging the tentacles while the others kept the Dark Young busy, I managed to make a good enough roll that Chekyl was able to set up a chain reaction that would blow up everything in the room, including the dome, while giving the party just enough time to grab the cultist's belongings and run for our lives.

So we just barely get out of range of the explosion, but we still have to keep running ahead of the wall of water that's now flowing after us, and the Dark Young isn't quite dead yet. So Elsbeth casts a spell to boost her speed and run on ahead, Ahsum and Janeath are carrying the trunk containing the cultist's things between them, and Chekyl is in the back trying to hold off the Dark Young with a Mi-go cold gun he'd picked up earlier, all the while praying he doesn't get grabbed by it.

By the time we make it about halfway back through the temple, two Mi-go that we had bypassed instead of fighting come out to try to hold us up. They don't have anything to worry about, because they don't have to breathe and are immune to cold, so they can afford to try to kill us. Somehow, we manage to avoid getting held up too much by them. Elsbeth moves around and gets chased by one while Janeath and Ahsum just bull-rush past the other, but Chekyl is far enough behind that even when he manages to finish off the Dark Young with the cold gun, he still has to struggle to keep ahead of the flood.

Now, fortunately, there are some branches in the path so there are a few areas where the water doesn't rush after them as fast as when it's a single path, and somehow Chekyl manages to keep from getting grappled and dragged to a watery demise. So we make it to the home stretch. Elsbeth has made it back to the submarine, and the Mi-go chasing her doesn't want to go into the water after her, because even though it can survive there, they apparently aren't good swimmers. (Plus, being a space-faring race, their preferred tolerance for atmospheric pressure is probably somewhere between 0 and 1.) So Janeath and Ahsum bull-rush it while carrying the trunk, knocking it prone, which Elsbeth follows up on by casting black tentacles to sprout out of the ground and hold it there.

Chekyl is still being chased by the other one, though, and it gets a lucky roll to grapple him. Now, Chekyl's not built for melee, and the only weapon he has in his hands at the moment is something that the Mi-go is immune to. So Ahsum lets Janeath take the trunk the rest of the way, and hurries back to knock it away from Chekyl so that they can resume their getaway, and we all manage to escape back into the sub right before the temple completely fills up with water and crumbles in on itself.

I was the GM, D&D 3.5.
The party was (mostly) sneaking around an underground ruin an evil cult had just started digging up. They heard that their really, REALLY powerful leader was there too, somewhere deeper down, but they didn't really worry about it.
The cult leader was a high-level wizard though, and the party was pretty low-level - they were supposed to avoid making a ruckus and sneak in and out before an alarm is raised.
In the end, they just decided to attack him, because hey, he can't be THAT strong, right?

I was pretty merciful, though, because the players complained they didn't get just how powerful the leader was... but it fit the situation anyways. Consider this:
- You're a high-level, prestigious wizard relaxing in a chamber of an ancient ruin, looking at the items your men dug up here. You're not really expecting trouble.
- Suddenly, your door is thrown open and a small bird bursts into your room! Before you can react, it rushes straight at you while shooting magical energy. This hit takes a third of your total hitpoints in a single attack. Behind this monster, an elf appears in the doorframe aiming a bow at you.
- Obviously you instantly teleport away, raising an alarm to evacuate afterwards. You only brought a bunch of workers and low-level guards, after all.

In the wizards mind, it must have been the insanely powerful pet of the elf who entered behind it, which would make the elf even more dangerous.

The wizard couldn't have known that the small bird was a full-fledged spellcaster/rogue who just sneak-attacked him with a low-level evocation and just rolled REALLY well (I think it was a crit, too...not sure anymore).

We're generally pretty good about not engaging things we can't beat handily. Even though half the party expected the half of us that engaged an antivehicular turret to be messily splattered, we blew it up without taking any damage... Unfortunately, the guy who dealt the killing blow -blew it up-, so we couldn't harvest the cannons.

But as for actually getting in over one's head... Have I mentioned the time a guy tried to Intimidate a heavily armed mercenary craft into giving him a ride without the shuttle fee?

5th edition party, GM running 1st edition module. We slaughter a party of gnolls on our way to the nearby town. At the town, the villagers talk about all the potential causes of the gnoll problem. We follow the trail that led directly to the end of the module. We sneak up on the exterior guards of this quarry, knock them out. However there are 8gnolls hiding in the tunnels with bows pointed outside. They are outside the range of party darkvision, so I, the monk, charge in the murderhole with a torch, so the ranger and the wizard can fuck them up. Wizard wastes her turn on invisibility instead of the fireball I was expecting, and the ranger is optimized for single target damage, because our normal DM loves big boss monsters. So I get skewered by the other 16 gnolls armed with spears and am only saved by the fighter hauling my ass back out.

So I was playing a 5th ed curse of strahd a week ago and we most of the party decided to not do any side quest so we were very low level.We were hired to find and retrieve some saint bones that got stolen from a church.We tracked the saint bones to a coffin maker's shop who we easily defeated.Turns out there were 6 vampire spawn on the second floor to say the least our 3rd level party had trouble.

3.5 Dragonlance campaign. Approximately 7th level. Party has been captured by a group of evil mages and left as a sacrifice to the local black dragon as part of the lease agreement on their temple. I'm playing the Kender rouge. Slipping the bonds is no trouble for me, I don't wear armor and they didn't find all of my knives. The rest of the party will take at least 10 minutes in game to get free, secure their gear, and equip armor.

In a fit of brilliance, I walk straight to the dragon's face and demand that he eat me because 'I've never been eaten by a dragon before and I think it would be a really cool thing to tell my friends back home about'. The dragon takes offense, refusing to eat something so low on the food chain. We argue for several minutes, ending in my character critting a grappel check and 'riding' the dragon through the swamp as it tries to dislodge me.

By the time I was finally thrown, the rest of the party was free, equipped, and fully buffed to send the dragon running.

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